potassium 5-{9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-1H-1,2,3,4-tetrazol-1-ide

• ChemBase ID: 153257
• Molecular Formular: C10H7KN6O
• Molecular Mass: 266.30048
• Monoisotopic Mass: 266.03184055
• SMILES: Cc1cccn2c1ncc(c2=O)c1[n-]nnn1.[K+]
• Canonical SMILES: Cc1cccn2c1ncc(c2=O)c1[n-]nnn1.[K+]
• InChI: InChI=1S/C10H7N6O.K/c1-6-3-2-4-16-9(6)11-5-7(10(16)17)8-12-14-15-13-8;/h2-5H,1H3;/q-1;+1
• InChIKey: NMMVKSMGBDRONO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: potassium 5-{9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-1H-1,2,3,4-tetrazol-1-ide
• IUPAC Traditional name: potassium 5-{9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-1H-1,2,3,4-tetrazol-1-ide; potassium 5-{9-methyl-4-oxopyrido[1,2-a]pyrimidin-3-yl}-1H-1,2,3,4-tetrazol-1-ide
• Synonyms: TWT-8152; Pemirolast (BMY 26517) potassium; 9-Methyl-3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one potassium salt; BMY 26517; Pemirolast potassium; 9-Methyl-3-(2H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one Potassium Salt; Alamast; Alegysal; BMY 26517; TBX; Pemirolast Potassium Salt

Database IDs

• CAS Number: 100299-08-9
• PubChem SID: 162247396
• PubChem CID: 443866

CALCULATED PROPERTIES

• Acid pKa: 2.6019034
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): -1.3553537
• LogD (pH = 7.4): -1.3764286
• Log P: 0.23503928
• Molar Refractivity: 64.0868 cm^3
• Polarizability: 21.595972 Å^3
• Polar Surface Area: 84.23 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: ≥18 mg/mL; Water
• Apperance: light yellow to yellow with a green cast powder; Pale Green Solid
• Melting Point: >280°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Histamine Receptor
• Mechanism of Action: Mast cell secretion inhibitor

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: K+; Potassium
• Application(s): Antiallergic agent; Used as K salt for the oral prophylaxis of asthma
• Empirical Formula (Hill Notation): C10H7N6O·K

DETAILS

Sigma Aldrich - SML0107

Biochem/physiol Actions
Pemirolast potassium is a histamine H1 antagonist and mast cell stabilizer that acts as an antiallergic agent. It Inhibits chemical mediator release from tissue mast cells and has recently also been shown to inhibit the release of peptides including substance P, neurokinin (NK) A, and calcitonin gene-related peptide (CGRP) from sensory nerves. It has been used for the treatment of allergic conjunctivitis prophylaxis of for pulmonary hypersensitivity reactions to drugs such as paclitaxel

Toronto Research Chemicals - P219800

Inhibitor of chemical mediator release from tissue mast cells. Antiallergic.

REFERENCES

• Cheng, H., et al.: J. Pharm. Sci., 76, 918 (1987)
• Yanagihara, Y., et al.: J. Pharmacol., 48, 91 (1987)
• Tinkelman, D.G., et al.: Ann. Allergy, 66, 162 (1987)
• U.S. Pat., 1978, 4 122 274; CA, 90, 103998u, (synth)
• Cheng, H. et al., J. Pharm. Sci., 1987, 76, 918, (hplc)
• Yanagihara, Y. et al., Jpn. J. Pharmacol., 1988, 48, 91; 103; 1989, 51, 83; 93, (pharmacol)
• Sano, A. et al., Chem. Pharm. Bull., 1995, 43, 683, (synth)